HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(Methylsulfonyl)aniline → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-methanesulfonyl-phenyl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(Methylsulfonyl)aniline | HCID 79617 | — |
| Reactant | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-methanesulfonyl-phenyl)-amine | HCID 59022984 | 51.5% |
Reaction Steps
A degassed mixture of 5,8-dibromo-imidazo[1,2-a]pyrazine (2.19 g, 7.916 mmol), 4-methylsulfonylaniline (1.49 g, 8.708 mmol), Pd2dba3 (145 mg, 0.15 mmol) and Xantphos (183 mg, 0.317 mmol), in dry toluene (50 mL) is stirred at 110° C. for 16 hours. After evaporation of the solvent, the residue is purified by silica gel column chromatography eluting with 95:5 DCM:NH3 (7M in MeOH). The title compound (1.496 g, 51%) is isolated containing some starting material (20%) and used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178530B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-6b12972455da4c48a1d5f3157de81b4e |
| Source note | uspto-grants-2012_05 |